Castle on the Hudson (1940)
Castle on the Hudson is a 1940 American drama film directed by Anatole Litvak and starring John Garfield, Ann Sheridan, and Pat O'Brien. A thief gets sent to Sing Sing Prison, where he is befriended by the reform-minded warden. The film was based on the book Twenty Thousand Years in Sing Sing, written by Lewis E. Lawes, who was in real life the warden of the notorious prison and did improve conditions for the inmates.
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